Enzymes
| UniProtKB help_outline | 798 proteins |
| Enzyme class help_outline |
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Reaction participants Show >> << Hide
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Namehelp_outline
apo-[alkylcobalamin reductase]
Identifier
RHEA-COMP:14731
Reactive part
help_outline
- Name help_outline an L-α amino acid residue Identifier CHEBI:83228 Charge 0 Formula C2H2NOR SMILEShelp_outline [*][C@H](N-*)C(-*)=O 2D coordinates Mol file for the small molecule Search links Involved in 566 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline glutathione Identifier CHEBI:57925 Charge -1 Formula C10H16N3O6S InChIKeyhelp_outline RWSXRVCMGQZWBV-WDSKDSINSA-M SMILEShelp_outline [NH3+][C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)[O-])C(=O)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 100 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline methylcob(III)alamin Identifier CHEBI:28115 (CAS: 13422-55-4) help_outline Charge 0 Formula C63H91CoN13O14P InChIKeyhelp_outline JEWJRMKHSMTXPP-WZHZPDAFSA-L SMILEShelp_outline [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]4[C@@H](O)[C@H](O[C@@H]4CO)n4c[n+](c5cc(C)c(C)cc45)[Co-3]456(C)N1C3=C(C)C1=[N+]4C(=CC3=[N+]5C(=C(C)C4=[N+]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
cob(I)alamin-[alkylcobalamin reductase]
Identifier
RHEA-COMP:14730
Reactive part
help_outline
- Name help_outline cob(I)alamin Identifier CHEBI:60488 Charge -1 Formula C62H88CoN13O14P InChIKeyhelp_outline OMAOKVYASDIYQG-DSRCUDDDSA-L Positionhelp_outline A SMILEShelp_outline [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]4[C@@H](O)[C@H](O[C@@H]4CO)n4c[n+](c5cc(C)c(C)cc45)[Co-4]456N1C3=C(C)C1=[N+]4C(=CC3=[N+]5C(=C(C)C4=[N+]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O 2D coordinates Mol file for the small molecule Search links Involved in 8 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline an L-α amino acid residue Identifier CHEBI:83228 Charge 0 Formula C2H2NOR Positionhelp_outline B SMILEShelp_outline [*][C@H](N-*)C(-*)=O 2D coordinates Mol file for the small molecule Search links Involved in 566 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline S-methyl glutathione Identifier CHEBI:141467 Charge -1 Formula C11H18N3O6S InChIKeyhelp_outline QTQDDTSVRVWHMO-BQBZGAKWSA-M SMILEShelp_outline [O-]C([C@H](CCC(N[C@H](C(NCC([O-])=O)=O)CSC)=O)[NH3+])=O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:63132 | RHEA:63133 | RHEA:63134 | RHEA:63135 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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| EC numbers help_outline |
Related reactions help_outline
More general form(s) of this reaction
Publications
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A human vitamin B12 trafficking protein uses glutathione transferase activity for processing alkylcobalamins.
Kim J., Hannibal L., Gherasim C., Jacobsen D.W., Banerjee R.
Pathways for tailoring and processing vitamins into active cofactor forms exist in mammals that are unable to synthesize these cofactors de novo. A prerequisite for intracellular tailoring of alkylcobalamins entering from the circulation is removal of the alkyl group to generate an intermediate th ... >> More
Pathways for tailoring and processing vitamins into active cofactor forms exist in mammals that are unable to synthesize these cofactors de novo. A prerequisite for intracellular tailoring of alkylcobalamins entering from the circulation is removal of the alkyl group to generate an intermediate that can subsequently be converted into the active cofactor forms. MMACHC, a cytosolic cobalamin trafficking chaperone, has been shown recently to catalyze a reductive decyanation reaction when it encounters cyanocobalamin. In this study, we demonstrate that this versatile protein catalyzes an entirely different chemical reaction with alkylcobalamins using the thiolate of glutathione for nucleophilic displacement to generate cob(I)alamin and the corresponding glutathione thioether. Biologically relevant thiols, e.g. cysteine and homocysteine, cannot substitute for glutathione. The catalytic turnover numbers for the dealkylation of methylcobalamin and 5'-deoxyadenosylcobalamin by MMACHC are 11.7 +/-0.2 and 0.174 +/-0.006 h(-1) at 20 degrees C, respectively. This glutathione transferase activity of MMACHC is reminiscent of the methyltransferase chemistry catalyzed by the vitamin B(12)-dependent methionine synthase and is impaired in the cblC group of inborn errors of cobalamin disorders. << Less
J. Biol. Chem. 284:33418-33424(2009) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.